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Chicago to Cayman Islands - Transfer & Transportation Guides

Find transfer & transportation guides from Chicago to Cayman Islands. How to get from Chicago to Cayman Islands by Flight.

You can get to Cayman Islands from Chicago by verhicle types below

Flight from Chicago to Cayman Islands
Search Transfer from Chicago to Cayman Islands

Transfer solutions

You have 3 options transfer to Cayman Islands from Chicago below

1. Fly from Chicago O'Hare
Subway ( 42 min. )

Take a subway from Jackson-Blue to O'Hare.

Open Map More details & check price at Chicago Transit (CTA)
Plane ( 3 hr. 47 min. )

Take a flight from Chicago O'Hare to Grand Cayman.

Open Map Check Flights
Walk ( 11 min. )

Take a foot from Grand Cayman to Airport Post Office.

Open Map
Bus ( 2 min. )

Take a bus from Airport Post Office to Agnes Way.

Open Map More details & check price at Grand Cayman Island Buses
Duration 6 hr. 50 min.
Distance 2627 km.
Cost 348 USD
2. Train to South Bend + fly
Train ( 2 hr. 25 min. )

Take a train from Van Buren St. to South Bend Airport.

Open Map More details & check price at South Shore Line
Plane ( 5 hr. 56 min. )

Take a flight from South Bend to Grand Cayman.

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Walk ( 11 min. )

Take a foot from Grand Cayman to Airport Post Office.

Open Map
Bus ( 2 min. )

Take a bus from Airport Post Office to Agnes Way.

Open Map More details & check price at Grand Cayman Island Buses
Duration 10 hr. 42 min.
Distance 2679 km.
Cost 497 USD
3. Train to Milwaukee + fly
Train ( 1 hr. 29 min. )

Take a train from Chicago Union Station to Milwaukee.

Open Map More details & check price at Amtrak
Bus ( 28 min. )

Take a bus from N6 & Clybourn to Airport.

Open Map More details & check price at Milwaukee County Transit
Plane ( 5 hr. 47 min. )

Take a flight from Milwaukee to Grand Cayman.

Open Map Check Flights
Walk ( 11 min. )

Take a foot from Grand Cayman to Airport Post Office.

Open Map
Bus ( 2 min. )

Take a bus from Airport Post Office to Agnes Way.

Open Map More details & check price at Grand Cayman Island Buses
Duration 10 hr. 16 min.
Distance 2856 km.
Cost 479 USD

Find Hotels in Cayman Islands

You can find hotels and accommodations in Cayman Islands with our hotels search tool below

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About Chicago, IL, USA

Chicago ( (listen), locally also ), officially the City of Chicago, is the most populous city in the U.S. state of Illinois, and the third-most-populous city in the United States. With an estimated population of 2,693,976 in 2019, it is also the most... Learn more

About Cayman Islands

The Cayman Islands ( or ) is an autonomous British Overseas Territory in the western Caribbean Sea. The 264-square-kilometre (102-square-mile) territory comprises the three islands of Grand Cayman, Cayman Brac and Little Cayman, which are located to ... Learn more

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